Reaction #4794

Reaction equation

2-methyl-4-nitropyridine-1-oxide

n-propanol

sodium

n-propanol

→

2-methyl-4-propoxypyridine-1-oxide

Conditions

Workup

1. 1
   Othern-propanol was evaporated off
2. 2
   workup.ADDITIONTo the residue was added chloroform under ice-
3. 3
   Temperaturecooling
4. 4
   Otherinsoluble materials were removed by means of celite filtration
5. 5
   OtherFrom the resultant solution was removed chloroform
6. 6
   Otherby evaporation
7. 7
   Washfollowed by elution with 10% methanol-chloroform

Procedure

To a solution of sodium n-propoxide solution prepared by dissolving sodium (1.7 g) in n-propanol (200 ml) was added to a hot solution of 2-methyl-4-nitropyridine-1-oxide (5.2 g) in n-propanol (210 ml). The mixture was stirred for ten minutes, then n-propanol was evaporated off. To the residue was added chloroform under ice-cooling, and insoluble materials were removed by means of celite filtration. From the resultant solution was removed chloroform by evaporation. The residue was subjected to a silica-gel column chromatography, followed by elution with 10% methanol-chloroform to yield 2-methyl-4-propoxypyridine-1-oxide (4.7 g) as an oily substance.

Source